7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-1H-<1>benzopyrano<4,3,2-ef><3>benzazepine

Base Information

• Chemical Name: 7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-1H-<1>benzopyrano<4,3,2-ef><3>benzazepine
• CAS No.: 154879-08-0
• Molecular Formula: C₂₆H₂₇NO₄
• Molecular Weight: 417.505

Synonyms:7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-1H-<1>benzopyrano<4,3,2-ef><3>benzazepine

Chemical Property of 7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-1H-<1>benzopyrano<4,3,2-ef><3>benzazepine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-1H-<1>benzopyrano<4,3,2-ef><3>benzazepine

There total 19 articles about 7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-1H-<1>benzopyrano<4,3,2-ef><3>benzazepine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-1H-<1>benzopyrano<4,3,2-ef><3>benzazepin-3-one (154879-07-9) → 7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-1H-<1>benzopyrano<4,3,2-ef><3>benzazepine (154879-08-0)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; benzene; for 26h; Heating;

DOI:10.1016/S0040-4020(01)81754-3

Reference yield:

ethyl 2-bromo-4,5-dimethoxy-α-(methylthio)phenylacetate (154878-94-1) → 7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-1H-<1>benzopyrano<4,3,2-ef><3>benzazepine (154879-08-0)

Guidance literature:

Multi-step reaction with 15 steps

1: 96 percent / Zn / acetic acid / 5 h / Heating

2: 61 percent / K₂CO₃, CuO / pyridine / 20 h / Heating

3: 76 percent / 1.) LDA; 2.) HMPA / hexane; tetrahydrofuran / 1.) -78 deg C, 30 min; 2.) -78 deg C, 30 min; 3.) RT, 1 h

4: 91 percent / NaIO₄ / H₂O; acetone / 15 h / Ambient temperature

5: 38 percent / trifluoroacetic anhydride (TFAA) / CH₂Cl₂ / 24 h / Ambient temperature

6: 66 percent / SnCl₄ / CH₂Cl₂ / 1.) 0 deg C, 1 h; 2.) RT, 6 h

7: 86 percent / H₂ / 5percent Pd/C / methanol / 168 h / at 6 kg/cm²

8: 92 percent / K₂CO₃ / acetone / 2 h / Heating

9: 92 percent / methanol / 5 h / 95 °C / sealed tube

10: BH₃*THF / 240 h / Heating

11: Et₃N / CH₂Cl₂ / 9 h / Ambient temperature

12: NAIO₄ / H₂O; methanol / 60 h / Ambient temperature

13: 95 percent / trifluoroacetic anhydride <(CF₃CO)2O> / CH₂Cl₂ / 59 h / Ambient temperature

14: 92 percent / Zn / acetic acid / 5 h / Heating

15: 62 percent / sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al) / benzene; toluene / 26 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; borane-THF; hydrogen; tin(IV) chloride; potassium carbonate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic anhydride; copper(II) oxide; zinc; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; acetic acid; acetone; toluene; benzene;

DOI:10.1016/S0040-4020(01)81754-3

Reference yield:

ethyl 2-<2-(benzyloxy)phenoxy>-4,5-dimethoxyphenylacetate (154878-95-2) → 7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-1H-<1>benzopyrano<4,3,2-ef><3>benzazepine (154879-08-0)

Guidance literature:

Multi-step reaction with 13 steps

1: 76 percent / 1.) LDA; 2.) HMPA / hexane; tetrahydrofuran / 1.) -78 deg C, 30 min; 2.) -78 deg C, 30 min; 3.) RT, 1 h

2: 91 percent / NaIO₄ / H₂O; acetone / 15 h / Ambient temperature

3: 38 percent / trifluoroacetic anhydride (TFAA) / CH₂Cl₂ / 24 h / Ambient temperature

4: 66 percent / SnCl₄ / CH₂Cl₂ / 1.) 0 deg C, 1 h; 2.) RT, 6 h

5: 86 percent / H₂ / 5percent Pd/C / methanol / 168 h / at 6 kg/cm²

6: 92 percent / K₂CO₃ / acetone / 2 h / Heating

7: 92 percent / methanol / 5 h / 95 °C / sealed tube

8: BH₃*THF / 240 h / Heating

9: Et₃N / CH₂Cl₂ / 9 h / Ambient temperature

10: NAIO₄ / H₂O; methanol / 60 h / Ambient temperature

11: 95 percent / trifluoroacetic anhydride <(CF₃CO)2O> / CH₂Cl₂ / 59 h / Ambient temperature

12: 92 percent / Zn / acetic acid / 5 h / Heating

13: 62 percent / sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al) / benzene; toluene / 26 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; borane-THF; hydrogen; tin(IV) chloride; potassium carbonate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic anhydride; zinc; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetic acid; acetone; toluene; benzene;

DOI:10.1016/S0040-4020(01)81754-3

upstream raw materials:

7-benzyloxy-2,3,4,12b-tetrahydro-10,11-dimethoxy-2-methyl-1H-<1>benzopyrano<4,3,2-ef><3>benzazepin-3-one

O-benzylcatechol

4-Bromoveratrole

ethyl (2-bromo-4,5-dimethoxyphenyl)acetate

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